Ammonia → HCID 22406767, compound

HRID 440480Notes

Reaction equation

HRID 440480 reaction equation
Cl.[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]([CH3:23])[CH:10]2[C:13]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:16][CH2:15][CH2:14]2)=[CH:5][CH:4]=1.N.C(OC(=O)C)(=O)C.[N+:32]([O-])([OH:34])=[O:33].C(=O)(O)[O-].[Na+].[C:41]([OH:46])(=[O:45])[C:42]([OH:44])=[O:43]>O.C(O)(=O)C.C(OCC)(=O)C>[C:41]([OH:46])(=[O:45])[C:42]([OH:44])=[O:43].[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]([CH3:23])[CH:10]2[C:13]2([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:14][CH2:15][CH2:16]2)=[CH:5][C:4]=1[N+:32]([O-:34])=[O:33]

Participants

10

Reactant 6

HCID 222AmmoniaHCID 944Nitric AcidHCID 971Oxalic AcidHCID 7918Acetic Anhydride2×HCID 516892Sodium BicarbonateHCID 22406817HCID 22406817, compound

Product 1

HCID 22406767HCID 22406767, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

The product of Example 41 (4 g) was dissolved in water at 80° C. The solution was basified with aqueous ammonia solution and extracted with ethyl acetate. The extract gave a residue which was dissolved in acetic acid (40 ml). The solution was cooled to 0° C. and acetic anhydride (20 ml) and then a mixture of 70% nitric acid (1.4 ml), acetic acid (30 ml) and acetic anhydride (20 ml) were added. The mixture was kept at 5° C. for 40 minutes and was then added to aqueous sodium bicarbonate and left for 16 hours before being extracted with ethyl acetate. The extract gave a residue which was purified by flash chromatography to give a solid which was dissolved in ethyl acetate. Addition of ethereal oxalic acid solution gave a solid which was triturated with hot ethyl acetate to give 7-hydroxy-2-methyl-6-nitro-1-(1-phenylcyclobutyl)-1,2,3,4-tetrahydroisoquinoline oxalate, m.p. 172°-173° C. (dec).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe extract gave a residue which
  3. additionwere added
  4. waitleft for 16 hours
  5. extractionbefore being extracted with ethyl acetate
  6. customThe extract gave a residue which
  7. customwas purified by flash chromatography
  8. customto give a solid which
  9. customgave a solid which
  10. customwas triturated with hot ethyl acetate

Sources & evidence

ORD record
ord-6f677612d7634de989b1938e16a7acee
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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